Ammonium formate → methyl 2-(5-hydroxy-1H-indol-1-yl)propanoate

HRID 734390노트

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HRID 734390 반응식
[CH3:1][O:2][C:3](=[O:23])[CH:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15]CC3C=CC=CC=3)=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:5].C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3](=[O:23])[CH:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:5]

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 578454965-Benzyloxy-indol-1-yl-propionic acid methyl ester

생성물 1

HCID 57845447methyl 2-(5-hydroxy-1H-indol-1-yl)propanoate

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매2회

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온도
60 °C

실험 절차

To a solution of 2-(5-benzyloxy-indol-1-yl)-propionic acid methyl ester (Example 3, 20.0 g, 64.7 mmol) in absolute ethanol (150 mL) was added Pd(OH)2 (2.0 g, 10 wt %) suspended in ethanol (50 mL). Ammonium formate (8.1 g, 129.3 mmol) was added and the resulting mixture was heated to 60° C. for 4 h. The reaction mixture was cooled to rt and the palladium was filtered through a plug of silica gel. The filtrate was concentrated to give a light yellow oil which was used in the following step without further purification (13 g, 92%). LC/MS m/z 220 (M+H)+, RT 8.01 min; 1H NMR (400 MHz, acetone-d6) δ 7.78 (br s, 1H), 7.28 (d, 1H), 7.20 (d, 1H), 6.97 (d, 1H), 6.77 (dd, 1H), 6.36 (d, 1H), 5.23 (q, 1H), 3.62 (s, 3H), 1.78 (d, 3H).

후처리

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationthe palladium was filtered through a plug of silica gel
  3. concentrationThe filtrate was concentrated
  4. customto give a light yellow oil which
  5. customwas used in the following step without further purification (13 g, 92%)
  6. customLC/MS m/z 220 (M+H)+, RT 8.01 min

출처 및 근거

ORD 기록
ord-bf3fcce48b7242f891bdecc986464af6
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592361B2

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